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4-Benzyloxyaniline hydrochloride → (4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-[1-(3-methyl-butyl)-piperidin-4-yl]-amine

HRID 1069179
ノート
印刷プレビュー

反応式

HRID 1069179 の反応式
C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[CH2:30](OC1C=CC(N)=CC=1)[C:31]1[CH:36]=[CH:35]C=C[CH:32]=1.[C:45](N1CCC(=O)CC1=C=O)([CH3:48])([CH3:47])[CH3:46].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O.C(Cl)Cl>[CH2:22]([O:21][C:18]1[CH:19]=[CH:20][C:15]([N:14]([CH2:35][CH:36]=[C:31]([CH3:30])[CH3:32])[CH:11]2[CH2:10][CH2:9][N:8]([CH2:6][CH2:46][CH:45]([CH3:48])[CH3:47])[CH2:13][CH2:12]2)=[CH:16][CH:17]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 27238314-Benzyloxyaniline hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 105479494-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl esterHCID 867570571-Tert-butyl-2-(oxomethylidene)piperidin-4-one

生成物 1

HCID 9910060(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-[1-(3-methyl-butyl)-piperidin-4-yl]-amine収率 94%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

The preparation of 4-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (Ia): 4-Benzyloxyaniline hydrochloride salt (10 g, 42.4 mmol) was suspended in EtOAc (500 mL) and washed three times with saturated sodium bicarbonate solution, once with brine, dried over Na2SO4, and concentrated. The free base was dissolved in CH2Cl2 (250 mL), treated with 1-tert-butyl-carbonyl-4-piperidone (8.45 g, 42.4 mmol), stirred for thirty minutes and then cooled to 0° C. NaBH(OAc)3 (13.5 g, 63.6 mmol) was added and the reaction was allowed to warm to room temperature and stir for eighteen hours. The reaction was diluted with CH2Cl2 (250 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated to give 15.3 g (94%) of the desired product. MS: 383 (M+1 for C23H30N2O3); TLC: SiO2, Rf0.39 (2:1 hexane/EtOAc).

後処理

  1. washwashed three times with saturated sodium bicarbonate solution
  2. dry with materialonce with brine, dried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionThe free base was dissolved in CH2Cl2 (250 mL)
  5. temperatureto warm to room temperature
  6. stirringstir for eighteen hours
  7. washwashed with saturated sodium bicarbonate solution and brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-151f9911070142fca7d8da217c08cf13
出典データセット
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06251919B1

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート